Great question about tax gain harvesting! I did this exact strategy last year when my income was low. Just want to emphasize a few key points that have been mentioned: 1. You can indeed buy back immediately - there's no waiting period for gains like there is for losses (wash sale rule) 2. The gain is locked in the moment you sell, regardless of when you repurchase 3. Make sure you're only doing this with long-term holdings (over 1 year) to qualify for the 0% capital gains rate One thing I'd add is to be strategic about which specific lots you're selling if you have multiple purchases of the same stock. You can use "specific identification" to choose exactly which shares to sell to maximize your tax benefit. Also, don't forget to factor in any transaction fees - while the tax savings are great, make sure the brokerage fees don't eat into your benefits too much. Good luck with your harvesting strategy! It's a smart move to take advantage of your low income year.

One additional consideration that might be helpful - if you're planning to do this regularly (not just this year), you might want to keep a spreadsheet tracking your cost basis adjustments. Each time you sell and rebuy, you're establishing a new cost basis for those shares, which will affect future tax calculations. For example, if you bought Stock XYZ at $50, it's now worth $80, and you sell and rebuy at $80, your new cost basis becomes $80. This "steps up" your basis and could reduce future capital gains when you eventually sell for good. Also, since you mentioned your income is around $22,000, you're well within the 0% bracket (which goes up to $44,625 for single filers in 2024), so you have plenty of room to harvest gains. Just make sure to account for any other income sources you might have throughout the year that could push you over that threshold. The strategy you're considering is really smart - taking advantage of low income years to realize gains tax-free is one of the best tax optimization moves you can make!

Has anyone used TurboTax to report a business sale? I'm trying to figure out if the self-employed version can handle this or if I need to upgrade to their business version?

I just went through this exact same situation when I sold my consulting firm last year. The key thing that helped me was understanding that you need to treat this as an asset sale, not a stock sale, which means each component of your business gets reported differently. For your client list and goodwill (the intangible value you built up over 8 years), these qualify as Section 197 intangibles and should be reported on Form 4797 Part I since you held them for more than a year. This gives you long-term capital gains treatment, which is much better than ordinary income rates. The installment sale aspect is important too - you'll definitely need Form 6252 to report the payments you'll receive over the next two years. This lets you spread out the tax liability rather than paying it all upfront on the 70% you received. One thing that caught me off guard was Form 8594 (Asset Acquisition Statement) - both you and the buyer need to file this with consistent asset allocations. Make sure your purchase agreement specifies how the sale price is allocated across different asset categories, or you might run into issues later. I'd strongly recommend getting professional help for this if you can. The classification of assets can make a huge difference in your tax bill, and there are specific rules about what qualifies for capital gains vs ordinary income treatment that aren't always intuitive.

If your cousin ever resurfaces and pays you back after you've claimed the bad debt deduction, you'll need to report that as income in the year you receive it (to the extent you received a tax benefit from the deduction). Just something to keep in mind.

I'm dealing with a similar situation right now - lent money to a family member who disappeared. One thing I learned from my tax preparer is that you should also keep records of any attempts to locate the debtor, not just collect from them. Screenshots of failed texts, returned mail, even notes about conversations with mutual contacts can help establish that the debt truly became uncollectible. Also, make sure you have clear documentation that this was actually a loan and not a gift. Bank records showing the transfer, any written agreements (even informal ones), and evidence that repayment was expected are crucial. The IRS sometimes challenges these deductions by claiming they were really gifts to family members. Having that promissory note you mentioned puts you in a much better position than most people in this situation.

Has anyone else noticed that the K-1 equivalent info from DST investments sometimes doesn't match up with the 1099-MISC? My DST sponsor sends a "Tax Information Statement" that shows different amounts than what's on my 1099. Confused about which numbers to use on my Schedule E.

Just wanted to add my experience with DST passive losses since I see a lot of confusion here. I've been invested in DSTs for about 4 years now and initially made the mistake of not properly tracking my suspended passive losses year over year. The key thing to understand is that these losses accumulate on Form 8582 if you don't have other passive income to offset them against. I learned this when I finally sold one of my DST interests and suddenly had a huge passive loss carryforward that I could finally use - it saved me thousands in taxes on the gain from the sale. Make sure you're keeping detailed records of your annual passive losses from each DST investment. When you eventually dispose of a DST interest (whether through sale or exchange), all those accumulated losses become deductible against any type of income, not just passive income. It's actually a pretty powerful tax planning tool once you understand how it works over the long term. Also, don't forget that if you do a 1031 exchange from your DST into another investment, the passive losses stay with you and continue to accumulate. Only an actual taxable sale triggers the release of all those suspended losses.

One thing nobody's mentioned yet - check if you might have been eligible for those contributions after all! I thought I had made excess Roth contributions for two years, but when I reviewed my tax returns more carefully, I realized my MAGI calculation was wrong. I had included some one-time items that shouldn't have been in the calculation, and I was actually under the limit for those years. Worth double-checking your MAGI calculation before going through the hassle of removing excess contributions. The definition of MAGI for Roth IRA purposes is pretty specific.

I went through this exact situation last year and want to emphasize how important it is to act quickly once you discover the excess contribution. The 6% penalty compounds year after year, so even though it seems small, it really adds up over time. One thing that caught me off guard was that when you remove the excess contribution, you also have to remove any earnings attributed to that excess amount. My IRA custodian had to do a specific calculation to determine what portion of my account's growth was tied to the excess contribution - it's not something you can easily calculate yourself. Also, make sure you specifically request a "return of excess contribution" from your custodian rather than just a regular withdrawal. The tax treatment is different, and you want it properly coded on the 1099-R they'll send you. The whole process took about 3 weeks from when I contacted them to when the money was removed from my account. Don't wait for the IRS to contact you - their automated systems will eventually flag this, and it's much better to be proactive about fixing it!